The Bert Show – Full Show PT 3: Thursday, January 8 [Vault]

Date: January 8, 2026
Cast: Bert, Kristin, Abby, Cassie, Tommy, and guests

Episode Overview

This episode of The Bert Show centers on two major themes: the incredible power of community as listeners rally to solve an international engagement ring disaster, and intimate behind-the-scenes drama from administrative assistants revealing workplace secrets. Alongside these stories, the show checks in with Dana—a 27-year-old woman in her first-ever relationship...with a 58-year-old man. As always, the Bert Show crew brings humor, warmth, curiosity, and a mix of skepticism and support to each subject.

Segment 1: The Engagement Ring Rescue – An International Feel-Good Story

Starts: [01:44]

Key Points

• The Incident: Laura shares a story about her friends from Scotland, Graham and Jenny. During their US visit, Graham proposed to Jenny, who then promptly lost the ring—down the defrost vent of Laura’s BMW. The cost to fetch the ring? $1,500–$3,000, possibly more than the ring itself.
• Community Support: The Bert Show listeners respond with offers for help, and expert mechanics volunteer to solve the problem.
• Reunion Planned: With the BMW dealership repair arranged, Graham calls in from Scotland to express gratitude.
• Potential Hand Delivery: A listener named Jill offers, by pure chance due to a golf trip, to deliver the ring to Scotland herself.

Notable Quotes & Moments

• On the mishap:
  Laura: “She puts it on her ring finger to show it to me and gestures and it flies off her finger and bounces off the windshield...and goes into the defrost vents of my car.” [02:11]
• On generosity:
  Graham (from Scotland): “I’m absolutely delighted and so happy that all the lovely people that have called in and made those offers… everyone has shown this morning has so humbled me. I’m just so happy.” [04:18]
• On cross-Atlantic camaraderie:
  Graham to Paul, the BMW manager: “The next time we’re in Atlanta, we’ll make a point of trying to meet up and I’ll get you a beer or two, or maybe three. And if you’re ever over in Scotland, then I would love to meet up and again, buy you a beer or two.” [05:55]
• On whiskey loyalty:
  Graham: “Whiskey as well should get a mention because it’s a very important part of our lives.” [06:24]
• On lesson learned:
  Graham’s advice: “If you’re going to surprise your girlfriend, you know, get the ring size first.” [07:41]
• On fate and delivery plans:
  Laura: “We’re gonna be there in 30 days, and I’m hand delivering it myself. We’re not letting this thing go anywhere else.” [09:49]
• The mechanic’s assurance:
  Paul (Global BMW): “We should have it out by tomorrow evening.” [10:40]

Memorable Vibe

This segment bursts with warmth, gratitude, and global connection, with laughs about accents and references to Scottish beer and whiskey. The listeners and crew turn a disaster into a heartwarming victory.

Segment 2: Dana’s Relationship Check-In—Age, Experience, and Promise Rings

Starts: [11:48]

Key Points

• Dana’s Background: 27 years old, never dated, now in a relationship with “Matlock,” a 58-year-old family friend.
• Rapid Progression: Since their first date, they’ve gotten serious fast—vacation plans (Bahamas), spending nearly every night together, and a promise ring.
• Concerns About the Relationship: The Bert Show hosts and listeners debate whether the issue is their 31-year age gap, or her complete inexperience.
• Friends and Family: Most friends and her parents are skeptical and hope it’s a phase. Dana insists she has agency and isn’t being manipulated.
• Workplace Role: Dana works independently as a buyer for a clothing store, dismissing accusations of gold-digging.

Notable Quotes & Moments

• Dana on her feelings:
  “I really didn’t believe that I would get all of this out of one date. And I just… I’m so in love with him… he’s so giving.” [12:29]
• On moving in:
  “We’ve been talking about moving in together and he’s even given me a promise ring, which is just incredible.” [14:53]
• Bert’s skepticism:
  “58 year old man giving you a promise ring?” [15:03]
• On skepticism from friends:
  “I have two friends that are really happy for me… but then I have other friends that really… are just skeptical and think that I’m gonna get my heart broken.” [18:38]
• Listener called “Terry” suspects Dana is a gold digger:
  “I think she is not as naive as you think. And I think she might be after poor man’s money.” [20:15]
• Dana’s response:
  “I’m doing well. I don’t need anybody to support me… I’ve never had a relationship. So if I wanted to be a gold digger, I could have done that years ago. Not what I’m after.” [20:35]
• Debate about promise rings:
  Co-host: “I think promise rings are full of crap.” [21:42]
  Bert: “Promise rings are okay if you’re 16. What do you mean they’re full of crap?” [21:46]

Memorable Vibe

It’s an honest, at times awkward discussion mixing supportive, teasing, and critical perspectives. The show balances concern for Dana’s situation with respect for her autonomy, wrapped in the show’s signature irreverence.

Segment 3: Administrative Assistants’ Deepest Boss Secrets—Voice Disguiser Confessions

Starts: [22:42]

Key Points

• Administrative Assistants’ Day: To honor assistants, the show invites them to share anonymously (with voice disguisers) the biggest secrets they know about their bosses.
• Scandalous Revelations: Assistants disclose affairs, illegal business activities, and private personal quirks about their bosses:
  • A consulting firm president fathered twins with a colleague as his wife gave birth.
  • A government employee is running his side business from his official role—possibly breaking the law.
  • An OBGYN is cheating on his wife (diagnosed with breast cancer) with a medical assistant, going so far as using a hidden credit card to pay her bills.
  • A metro mayor runs personal affairs during office hours.
  • A senior VP is having a romantic affair with another man he hired, unbeknownst to his wife.
  • A boss keeps size 12 red stiletto pumps and a black leather sock in his desk drawer.
• Insight Into the Role: The show emphasizes why assistants are so valuable and why bosses should never underestimate them.

Notable Quotes & Moments

• On assistants knowing it all:
  Co-host Cassie: “The voice disguiser really is a beautiful, beautiful device… There’s no accountability there.” [23:23]
• Affair revelation:
  Caller: “And as his wife gave birth to a little boy, this attorney in another state also became pregnant with twins and she was unmarried.” [24:17]
• On workplace crime:
  Caller: “My boss is running his personal business through the government. Highly illegal.” [25:41]
• On the OBGYN cheating scandal:
  Caller: “He has us pay her [the medical assistant’s] bills with his credit card while his wife is sick, in bed with breast cancer.” [28:31]
• On a same-sex workplace affair:
  Caller: “Turns out the guy [my boss is having an affair with] just got hired for a major project.” [33:31]
• Cross-dressing hint:
  Caller Sally: “He keeps a size 12 pair of ladies red 6 inch stiletto pumps in his office drawer, locked, along with a black leather sock.” [34:13]
• On the value of assistants:
  Co-host: “You need to freaking honor your administrative assistants because they know everything.” [31:06]

Memorable Vibe

This segment is juicy, light-hearted, occasionally jaw-dropping, and hilarious, offering a dose of schadenfreude and a reminder never to underestimate the keepers of office secrets.

Timestamps for Key Segments

• [01:44] Engagement Ring Incident Setup
• [04:14] Graham from Scotland Joins the Call
• [06:24] Scottish Whiskey & Engagement Ring Story
• [11:48] Dana’s Relationship Check-In Begins
• [12:29] Recap of Dana’s Progress with “Matlock”
• [17:12] Hosts Voice Concerns; Dana Defends Herself
• [20:15] Call-ins: Gold Digger Accusation
• [21:42] Promise Ring Discussion
• [22:42] Admin Assistant Secret Confessions Begin
• [24:15] The Secret Twin Affair Story
• [25:41] Government Work Misuse
• [27:28] OBGYN Cheating on Wife with Cancer
• [33:31] Senior VP’s Office Romance Exposed
• [34:13] The Red Stilettos Closet Secret

Conclusion

This episode delivers classic Bert Show fun—relatable drama, wit, and a peek into other people’s lives. There's an infectious sense of community (whether crowdsourcing a BMW repair or examining relationship red flags) and enough behind-the-scenes office gossip to enthrall any listener. The hosts’ blend of skepticism, empathy, and sarcasm keeps things moving, authentic, and entertaining throughout.